A new method for the synthesis of diamantane by hydroisomerization of binor-S on treatment with sulfuric acid

Rishat I Aminov; Ravil I Khusnutdinov

doi:10.3762/bjoc.16.205

A new method for the synthesis of diamantane by hydroisomerization of binor-S on treatment with sulfuric acid

Beilstein J Org Chem. 2020 Oct 12:16:2534-2539. doi: 10.3762/bjoc.16.205. eCollection 2020.

Authors

Rishat I Aminov¹, Ravil I Khusnutdinov¹

Affiliation

¹ Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, pr. Oktyabrya 141, Ufa, 450075, Russian Federation.

Abstract

A new method was developed for the direct synthesis of the second representative of the homologous series of diamond-like hydrocarbons, diamantane, in 65% yield by hydroisomerization of the norbornadiene dimer, endo-endo-heptacyclo[8.4.0.0^2,12.0^3,8.0^4,6.0^5,9.0^11,13]tetradecane (binor-S) on treatment with concentrated sulfuric acid (98%). In the presence of H₂SO₄ of lower concentration (75-80%), the reaction stops after the hydrogenation step giving endo-endo-pentacyclo[7.3.1.1^2,5.1^8,10.0^3,7]tetradecane in 68% yield with excellent selectivity (100%).

Keywords: binor-S; diamantane; hydroisomerization; sulfuric acid; tetrahydrobinor-S.

Grants and funding

The results were obtained with the financial support of the Russian Ministry of Education and Science (project no. 2019-05-595-000-058) on unique equipment at the 'Agidel' Collective Usage Center (Ufa Federal Research Center, Russian Academy of Sciences), by the Scholarship of the President of the Russian Federation to young scientists and postgraduates (SP-1601.2018.1) and carried out within the RF state assignment, reg. no. АААА-А19-119022290009-3.